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Now why would I do such a thing?

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60

Maybe

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51

The Cuckysitter is making sure that the cuckold's time under Her care is eventful and rewarding. She wants to be the best.

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16

Ass-slave conditioning.

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94

Balcony neighbor

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87

What am I going to do with you?

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108

DECORATING FOR THE HOLIDAY [Darkest-Muses]

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47

Amouranth loves that you can work from home

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18

Did mommy give you permission?

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19

thank you dear

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34

It's just the right thing for a beta like you! Chastity for you, big cock for me

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36

A New World Femdon Society

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25

you will finish locktober for them

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16

365 days to go

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15

I'm tempted

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32

It's only October 5th..

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33

All day. After several hours you'll be utterly soaked, which will provide Her with more lubrication. And it is very hard to breathe through that.

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27

Goon marathon

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50

The taste of her ass is just too good!

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51

Do you see chastity as a sexual meditation?

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74

Goth GF

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284

Another challenge

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59

So dumb, so Desperate.

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53

What a thoughtful keyholder!

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30

Complaining is unacceptable behavior.

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64

I love teasing you while your in chasity

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20

Use her vibrator to SQUIRT

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20

Chastity is the best thing for you.

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57

No hard feelings

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59

You booked and paid for a week long all-inclusive trip at the beach for you and your girlfriend hoping it would earn you some sort of release. Unfortunately for you, she had other ideas...

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88

Servitude is the only logical option for weak beta men..

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138

You look forward to your birthday because you know youll finally get released. This year your desperation got the better of you... and your girlfriend is not the forgiving kind....

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99

Better then any release could have been

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34

Metal Friend

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32

She's going to have so much fun with you.

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34

SIGN LANGUAGE [Darkest-Muses]

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24

He will be blown away!

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53

the beautiful sound of the padlock closing

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15

How lucky you are to get to worship Me.

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29

I have your dicks life hanging by my tits

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18

Your keyholder is very easily distracted.

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75

I love blowjobs but definitely not with little dicks!

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28

not a nightmare

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47

Your poor morning wood

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36

Blowjob

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43

New University Rules

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122

Cruel girlfriend Marya

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154

St. Chastity Boarding School

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13

Remember...

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64

There, all nice and put away in a safe place. A safe place you will never experience again because everyone knows.

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28

Your honeymoon isnt going as planned...

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71

A fair trade offer

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394

October is Locktober for you

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62

You asked your friend to hold your keys for locktober

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107

It is best to not touch the cage in any way, It is best to not do anything that might be seen by cameras, hidden or otherwise. The consequences could be severe.

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14

First caption (not me in pic)

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34

Rita Ora extends your chastity sentence

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41

It's simple, Really.

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23

What you want is not important to her...

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72

Flashing at the fast food place

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55